Chapter 4 - "Hell"oween

Becky found herself a torrent of emotions as she had her hair and makeup being done by one of the sorority presidents. Even though the makeup was only the lower part of her face and neck, she felt more glamorous than she had ever felt in her entire life. She was also mostly naked and knew she would be spending the rest of the night that way in front of a ton of complete strangers.

Well, that wasn’t truly accurate. She did have the mask that obscured most of her face, and the makeup was doing more. Her hair, with some blonde streaks added, was down and would be covering her breasts when all was said and done, and she did have on the ribbony skirt that went all the way down her legs, but too much movement would be all too revealing.

Becky still didn’t understand how she was stuck in this situation. There were four frats and five sororities on her campus, and for the Halloween party, each had to provide a girl to be part of the entertainment for the party. The sororities had it easy, they always volunteered freshman pledges for it. The frats had to find a girl, and apparently, it was Trip who was selected to find a girl, and Becky was his go-to girl.

The girl doing her makeup set the brushes down after a last little dusting of her chin and moved Becky’s hair to flow down over her tiny breasts. She turned Becky toward the mirror and Becky was shocked, she had never seen herself looking so hot, even as half her features were hidden.

As Becky looked agape, the girl doing her makeup smiled and looked around the room, where eight other girls had their makeup and costuming done to be similar to Becky’s.

“Right on time,” she said to Becky before turning her back around in the chair. Becky noticed all the other girls were also being turned around to face the entrance of the room, where another one of the sorority presidents was walking in.

“Alright ladies,” the new president, who Becky was kind of sure was named Kathryn, called out, “here’s what’s going to happen tonight.”

Becky’s heart raced, she knew that nudity and the chance of sex were on the table thanks to Trip, but she didn’t know what it meant, and she was a little afraid to find out.

“So mermaids, you’ll all be on one of the walls near where we have some of the kegs set up. Every guy will get a ticket, which they can use to make a guess. With your makeup, your lack of clothing, and of course your mask, the idea is that each guy can take a single guess at who you are. You’re all freshman, so most of you should be fine with nobody knowing who you are. Except for you Jessica.”

Kathryn had laughed and was looking at a girl near her with lightly tanned skin, very blonde hair, and fairly large breasts. The girl named Jessica seemed to laugh as well.

“Now of course the catch is, each guy only gets one guess with a single girl. He’s wrong, and he gets nothing. He doesn’t get to try with another one, just one attempt.”

The silence when she paused creeped Becky out. The obvious question to be asked hung in the air, yet all of the girls were remaining silent.

“But if he knows it’s you and guesses correctly, then quite simply he gets you.” Kathryn waited for a three-count before continuing. “We have rooms set up and you’ll go there with the lucky guy and they get half an hour with you, they’re in charge. You can try and manipulate the guys and seduce them into what you want to do ... but the reality is it’s mostly senior guys at this party so you better be prepared to have sore assholes for the next few days.”

A quiet murmur started among the other girls. She suspected that a few of them had never had it up the butt before, and Becky found herself sighing as she realized that anal sex was now the majority of her sexual experiences.

“Alright ladies, settle down,” Kathryn called out. “When your time is up, you’ll head back here to have makeup touched up. Also, after a guy has successfully gotten the chance to use you, your costume changes.”

Everything was quiet once more and all the girls were paying attention again.

“The first time, your hair gets pulled back into a ponytail for the rest of the night. Yes, that means you’ll be going around topless. The second time you lose the skirt, so only the mask, and the third time if guys get that far, you lose the mask and undergo a costume change. Yes, you’ll have to stay fully naked, but certain accessories will enhance your look and I’ll leave it at that.

“Also, at just before eleven, any girls in the alternate costume may be involved in a little show. The show will accommodate up to three of you so you should really hope that either you don’t get stripped, or if you do at least three other girls get stripped as well.”

With a smile that Becky felt was just a bit sinister, Kathryn finished with “Now let’s finish getting you ready, your horny crowd awaits.”

The party and Becky’s part in it had started a little over an hour prior, and so far she had been lucky. Only three guys had tried to guess her identity, and so far none of them were right.

Becky watched as Jessica, the girl called out about being well known was already down to just her mask and she had another guy talking to her. Becky shook her head in amazement as she watched Jessica nod to the guy and head off with him. Becky was one of four girls who hadn’t had to go back with any guy yet, and here this girl was already tapped out—quite literally even.

As she saw Jessica walking off, she turned to look back forward and saw someone coming toward her. Under the mask her eyes went wide—she thought she recognized the guy as he looked like someone who lived in a room just down the hallway from her. If it was him she would have been really surprised, he always seemed rather shy and super-introverted.

The guy she thought was Patrick from her dorm leaned in to whisper to her as was custom.

“Are you by chance Becky?”

Becky gulped and nodded, she reached down and grabbed his hand, and pulled him along with her to one of the rooms reserved for this. The guys who were standing guard outside the rooms nodded and motioned to one of the empty rooms. Leading Patrick inside, she closed the door behind them.

“Can you take everything off?” Patrick asked of her.

Becky nodded and removed her mask and let the skirt fall to the floor. “For the next half-hour, you get whatever you want.”

For the first time, Patrick smiled and approached her. Becky felt her heart race, wondering how this was going to go down.

Patrick reached his arms around her and came in to kiss her. She wasn’t gonna lie, as his lips touched hers she definitely felt it was the most awkward kiss she had ever experienced. As his hands moved down her body and grabbed her ass, she was a bit surprised.

He broke the kiss and said, “I’d like you to kiss me down there.”

Becky gave her best smile and nodded. Dropping slowly to her knees, she was once again surprised when he quickly undid his pants and pulled them and his tidy whities down, revealing a fairly average-sized cock that Becky found herself kind of relieved to see. Both Trip and Jake had been much larger and in some twisted way, this would give her some small relief. As she looked closer she was a bit startled to realize that his cock had looked different than all the others she had seen—Patrick was uncut, a definite change for the teenage girl.

Taking a deep breath she reached out with her right hand and grabbed the base of his cock to steady it.

“Wait,” he said suddenly and Becky pulled back his hand. He was looking intently at the desk that was behind Becky and she turned around to look at it. Much to her surprise and horror, the table was covered with all sorts of sex toys.

Patrick held a hand out to pull Becky up and she went along with it. Walking her over to the desk, he looked at her and asked, “Do you think these are for our use?”

Becky wasn’t sure, she didn’t know whose room this was, but as she looked at the assortment of toys scattered on the table she saw the notecard in the corner.

‘For use during the party. —enjoy!’

Becky nodded and pointed to the note. Once he saw it, Patrick didn’t hesitate at all as he picked up a small, bright purple tubular vibrator off the table and held it out.

“Can you please suck on this for a moment?”

It was weird knowing that Patrick could do whatever he wanted within reason yet he was still being so shy and polite about it. Despite the oddity of it all, Becky nodded and took the vibrator from him and started pushing into her mouth, working to slobber all over it as though she were giving a messy blowjob. She wasn’t a dummy, she knew he’d soon be using it on her and she would want it as slick as possible.

Patrick smiled at her with a creepy intensity as she blew the smooth vibrator. Becky knew that he was probably imagining when she would be doing that to him in a moment. When he finally reached out his hand for the vibrator Becky once again found herself being apprehensive.

“Can you please get on your knees and bend over the bed, then keep looking forward?” Patrick asked, still sounding nervous despite the control he was clearly in.

“Of course,” Becky responded with a smile. Maybe if she was pretty compliant she might get off easily. The girl made her way over to the bed and dropped once more to her knees, bending over the bed and spreading her legs so he could insert the vibrator from behind.

She waited. And she felt like she kept waiting as she heard some rummaging behind her for a moment. She was trying to be obedient, but curiosity was threatening her ability to do so.

Finally, she realized that he was right behind her and had knelt down on the ground himself. The moment arrived and she felt a little jolt as she felt the hard plastic press against her asshole.

‘Of course, he’s sticking it up my ass,’ Becky thought wryly. The hard plastic penetrated her hole and slipped deeper into her rectum, a combination of her spit lube and the stretching the tiny hole had experienced in the two months she had been at school.

To Becky, it didn’t hurt per se, not like it used to, but it was definitely still an intrusion and still left her with that full feeling she had when Trip took her anally.

With the tube nestled firmly in her bowels, he twisted the end to turn it on to vibrate, and Becky let out a reflexive “Ooh!” of surprise.

“I always wanted to stick something up a girl’s butt,” Patrick told her in a tone of voice that sounded more like he was talking about the weather. Small talk about things going in her ass wasn’t exactly Becky’s forte, and she made sure to keep her thoughts of ‘That could have been your cock, you know?’ to herself.

Becky just nodded before he added, “And now you can go ahead and suck me.”

She knelt up from the bed, a little slow to allow her body to adjust to the intruder. She only had to turn a little bit to face him, and she was instantly crestfallen when she did. His cock was now rock hard, but it was the cell phone in his hand that broke her. He was going to record this. Or maybe he had already started recording as the vibe got shoved through her back door ... either way, she knew this wasn’t a good omen.

Once more Becky reached out and grabbed the base of his cock to steady it before leaning closer and taking it into her warm, waiting mouth. His foreskin was a significantly different feeling to Becky, and she was unsure what to make of it.

Patrick moaned and managed to say, “Look at me!”, as she was backing off. Becky looked up, expecting to make eye contact, but instead, she was finding herself looking into his phone’s camera. She slow blinked a couple of times as she internally sighed, but she slowly got back to work, looking mostly at the phone as she did so. Becky made sure to suck on his cock in a slow, methodical way—she knew time was relatively short and she hoped that a blowjob and a toy up the ass could be the only real event.

Even as she was looking up, Becky found herself losing track of time as she continued the slow, sensual blowjob. At least Patrick was the type of guy who didn’t realize what it was that she was doing, so when the five-minute knock on the door came, she was excited that it was almost over.

Patrick was apparently excited too as he suddenly reached down with the hand not holding the phone and yanked her head back and let out a low grunt. Becky was once more taken by surprise at how quickly things went from the five-minute knock to having hot cum shot onto her face.

Even more so was how much he was shooting out—four thick ropes had covered her face before he aimed and shot the rest into her mouth, nearly filling it as well. She had to swallow a few times and he didn’t seem to react to that like she thought she might.

When he was down to a dribble he groaned out “clean me”, bringing the phone closer as Becky pulled back his foreskin and polished off the head of his cock. Once she pulled off he held out his free hand to help her stand.

Once she was standing, he reached down to her pussy and slipped a finger inside rather easily. “You’re very wet, I’m glad you enjoyed that!”

Becky could only hesitantly smile in response. It was awkward standing there before him naked, the vibrator still working in her ass and face covered with cum. Patrick motioned for her to turn around, and she did. He pushed his free hand on her back and she bent down toward the bed. She felt the vibrator turn off and the tug of the vibe as it was slid out of her ass.

At the moment it fell out of her ass the door open and one of the guys acting as a guard said, “Time’s up!”

Patrick dropped the vibe that was in her ass onto the floor with a clatter, and he smiled at her. “Thank you, I really enjoyed that. I hope we can do that again in the future.”

Another furtive smile from Becky. She resisted the snark to express her thoughts of ‘with you having that video, I imagine we will.’ More than anything though, Becky was disappointed, before tonight, she could have imagined herself dating Patrick if she weren’t with Trip, but now the sweet innocent veneer had been stripped forever.

Picking up her mask and skirt, she covered herself and the guard walked with her in the back hallways so she can have her hair and makeup redone.

A little bit of facial scrub and Becky was back In the makeup chair getting the finishing touches applied. Her skirt was back on and her hair was now pulled back—the rest of the night she would be topless as she waited to see if she would have to get anyone else off.

There wasn’t much conversation before she was led back out to the staging area. When she got there she noticed several things at once.

Jessica wasn’t amongst the girls, in fact, she was out in the party, naked with cat ears and a tail coming off her butt. It took her a moment to realize that the tail was actually coming out of her butt and what that all implied. She realized that if she were to be taken 2 more times that she would probably end up the same way.

She also noticed that two other girls were down to just their masks, and another girl was topless like her, two other girls were completely untouched still, and two who were currently gone. Having been escorted back out, she resumed her spot for what hopefully would be an otherwise boring evening spent mostly naked at a party.

Unfortunately for Becky, that didn’t seem like it was going to be the case. Not even a minute after she had returned to the lineup, she had another potential guesser sauntering his way up.

Becky was confused, she was sure that she had never seen this guy before in her life; he didn’t look like anyone from classes, nobody she had seen around Trip’s fraternity, and no one she knew from outside of school. So why was he approaching her like a cat that swallowed a canary?

Like Patrick before him, this unknown guy leaned in and whispered, “Hello Becky.”

She froze, except for her eyes going wide in fear. How did this guy know who she was? The stranger didn’t even wait for her to respond, he grabbed her hand and just started pulling her away. She was in a daze, and as she remembered the job she had, she finally grabbed the guy’s hand back and led him to the same room where she had just blown Patrick.

The only thing that had changed since she was last in the room is the vibe that had previously been in her ass was back on the desk, otherwise, it looked just like when she entered it earlier.

“Strip bitch, then lay down on your belly on the bed, head hanging over the end.”

Becky thought that her capacity for surprise would have been exhausted already, the stranger’s demeanor, and his command to her had taken her aback.

With that though, Becky obeyed and quickly dropped the skirt and the mask to the floor, once more naked with a guy, though this one a complete stranger still as far as she could tell.

“Can I...” Becky started to ask, but the stranger immediately snapped, “No talking unless you’re told to, understood?”

A little fearful of making him mad, she just nodded vigorously as she headed to the bed. She climbed on and laid down the way he had instructed her to.

“Alright, spread your legs a bit, bend at the knee and reach back and grab your heels.”

Becky did as commanded, though she found it a bit awkward to do so. In grabbing her heels, she felt that she had to pull her chest up off the bed to make it work. As she looked back around at herself, she realized that she had seen this position before in porn videos. She felt a bit more dejected once realizing that she was truly being used as a sex object now.

It was in that thinking time that Becky didn’t notice the stranger had opened his pants, revealing a rather sizable cock. Probably number three in size of guys she had experienced, right after Jake and Trip. He stepped up to her, his cock standing at attention before her eyes. He grabbed her hair with a hard yank, a cry escaping her lips for only a second before his cock was shoved between them.

The stranger wasted no time; by the time she would have begun really working on giving head if she were in charge he already had thrust in and out of her mouth ten times. This was definitely a porno moment for her, she wasn’t giving head she realized; she was getting face-fucked.

Becky felt lower than she ever had. Even with the times that Trip had buttfucked her, being three-holed by Jake, and even the weird anal toy blow job she had given Patrick, none of these actions made her feel the way she did now with this stranger’s cock being thrust into her mouth, near the point of gagging. The way he held her head and the very submissive position he made her take the facefucking in was truly getting to Becky in a way she hadn’t thought possible.

This was Becky’s slut moment—no, worse than that, this was the moment Becky felt like an object, just a hole for a guy to use to jack off. Her mind was completely detached from the situation. She wasn’t really registering much of the effect that the cock thrusting in and out of her body was having, or even how long it had been doing so. Even worse was when she completely missed that it was no longer inside her mouth and the stranger slapped her face.

“Wow, in the slut zone just from a face fucking huh? I know exactly what to do with a horny little bitch like you.”

Becky couldn’t believe how much this stranger had completely misunderstood her being disassociated. Before she could protest, the facefucking stranger gave his next command.

“Get up, turn around and put your knees at the edge of the bed. I want you face down ass up.”

At least Becky couldn’t have any mistake of what he expected of his temporary flesh doll. She released her ankles and pushed herself up off the bed, her muscles a little tense after how she held herself. It was only now that she realized how much of her own spit was running down her face. Disgusted, she didn’t bother looking at the stranger as she turned around and started to kneel at the edge of the bed. Becky leaned forward, getting on all fours before lowering her torso to the bed.

“Arch your back more!” It definitely came as a command and with her head facing toward the door, she lowered her face and shoulders to the mattress, trying to push her back down and her ass up.

“I’m glad you’re being an obedient little cunt, Becky.”

She wished she knew who this guy was, did she know him from somewhere? He seemed older so she didn’t think she had a class with him. She didn’t remember seeing him around Trip’s frat.

Her thinking about how she was identified by him was interrupted by his left hand firmly grabbing her left hip, but even more so as she felt the tip of his cock pressing against her back door.

Even the process of her thinking ‘oh no, not my ass’ was paused by the way the stranger forcefully violated her asshole with his cock. Once the tip was in his right hand grabbed her other hip and he pulled her slightly sore hole deeper over his cock.

Becky let out an involuntary cry. Yes, she had gotten used to anal thanks to Trip and the butt plug, but it had been a while since she had it as rough as this guy was making it. For the most part Trip, and even her experience with Jake, seemed to take care of things, knowing that if she was pushed too hard she might say enough is enough. This guy however got up to speed and started pounding her ass as though there was no tomorrow—and he was probably right in that this would be his only chance to fuck her ass and he was going to take it.

Becky’s pained yelps continued as he built a fast rhythm fucking her ass. Without a doubt, this was the most brutal buttfucking she had experienced so far.

The stranger was a machine, he just kept postponing in and out of her tightest and what should be her most private hole with zero remorse. Becky tried to concentrate on something, on anything else, but the fire of her asshole burning from friction prevented her from doing so.

It was only the five-minute warning knock that brought any distraction from how raw her ass was feeling. She couldn’t believe it, there was no way that between her mouth and her ass that he had been pounding her holes for twenty-five minutes already.

Suddenly he stopped to Becky’s complete astonishment, but no time to think about it was given as he pulled her legs off the bed and she quickly collapsed into it, her knees hitting the ground with a thud. He grabbed her arm aggressively and turned her over, her body collapsing to the floor as she sat against the foot of the bed.

The stranger clasped her hair in his hand and pulled, eliciting another cry from the girl. The cry was quickly muffled as he shoved his cock back in her mouth and thrust her head on his shaft only a few times before both his hands held her head tightly to his crotch. Becky panicked as his hot cum flooded her throat suddenly, she had no choice but to swallow to keep from choking on the thick, sticky goo.

He held her there like that for a solid minute, grunting with every twitch of his cock that pumped more cum down her throat, and the few times he jerked her head a bit more. When he started to soften he gave her his final command.

“Lick me clean.”

Becky started swirling her tongue, trying to bathe his cock with it before she had the realization—his cock went straight from her ass back into her mouth. She wanted to vomit at the thought that she was tasting her own ass off his dick. A jerk of her head from his hands reminded her to get back to work.

“Come on, I might have a chance to score before the night is over and I don’t need my cock tasting or smelling like your wrecked little ass.”

This was a new low for Becky. She couldn’t believe it. She sighed and resumed her licking. Finally, after another minute he let go of her head and let his flaccid cock out of her mouth.

Completely disgusted, she asked, “Who are you? And why?”

Before the stranger could answer one of the guys acting as a guard opened the door and said “Time’s up.”

The stranger just grinned and left, grabbing her skirt and taking it with him as a prize of war.

Becky started to pick herself up and she felt every inch of the pounding she had just taken through her body. Her ass was sore, her mouth was sore, and she knew she still had to go back out there.

She passed a mirror as she left and noticed how messed up her makeup was, not just from below her mouth, but her eye makeup was destroyed too. Becky grabbed her mask off the floor and covered her face.

Slowly with her escort, she made her way to the makeup room. The girl who ended up doing her makeup just shook her head and said, “Rough one I see.”

All Becky could do was nod. Two of the other girls were in the room at the same time, and both were a little antsy in their seats.

“I always heard that anal hurt the first time, but I don’t think I’ve ever even had it that hard in my pussy.”

“I know what you mean, these guys aren’t here to play. I’ve only had one guy and he just lubed up and attacked my ass.”

“You’re lucky it’s only been one. I’ve had two and they’ve both done it to me. What about you?”

It took Becky a second of overhearing their conversation before she realized that they were both looking at her.

“Oh, um, the first guy just stuck a toy up my ass the whole time, the second guy fucked my ass hard. I’ve had anal before tonight, but not like that.”

The other girls nodded in solidarity to her. The girl who only had the one guy so far got her skirt fixed and headed back out. The second girl went out with only her mask not long after. Becky closed her eyes and tried to just let her body rest, knowing she would be going back out there any moment.

Becky’s bliss was short-lived as she was soon having the mermaid mask fit over the top half of her face. Becky got up and the girl gave her bare ass a slap. “Good luck out there.”

Luck, luck was what Becky would need to not have to be out in front of the party and to not be unmasked. When she did get to her spot, the girl who was in the makeup room without a skirt was still there, but the girl who had only had one guy was now being led off to the rooms.

Becky turned to look forward and her face immediately fell. With a cocky smile even worse than the stranger who just used her, Jake was walking up.

Leaning in, he whispered, “I saw you earlier, but you were taken before I could get over here. I just knew I needed another shot with you.”

‘We’ll fuck, used three times,’ Becky thought. She wasn’t sure what she was feeling. She knew that being used three times made her eligible for the show at the end of the night and that was a quite upsetting thought for her. As for it being Jake, she really was unsure about that—on one hand, at least she was only getting fucked by two new people, on the other hand, Jake fucking her again wasn’t something she liked the idea of encouraging.

She simply nodded to him and reached out her hand and off they went, for the third time in under 2 hours Becky was going to find herself back in the room getting fucked.

They entered end Becky took off her mask. Still holding her hand, Jake dragged her over to the table of toys. He smiled as he looked over the table before releasing her hand. He picked up what mostly looked like a leather strap, but with a light tan thing hanging off it.

It was only when he held it before her that Becky realized it was shaped like a short penis, and that the leather strap had a buckle on one end and holes on the other.

“Open wide,” Jake commanded. She did so and he brought the strap to her face, pushing the rubbery dildo bit inside her mouth. He pulled the straps against her head and worked on the buckle. That’s when it hit Becky--Jake was using a gag on her, a gag with a cock on it.

It had only been in a few seconds and Becky realized that she didn’t like how this rubber dick was holding her jaw open. It was a different kind of humiliating than what she had experienced so far this night.

Jake returned to the table and watched as he picked up some weird-looking toy, it was mostly hot pink and looked like a curved vibrator, but it had a second, claw-like appendage sticking out near the end that she wasn’t sure what that was about. He set down the toy near the edge of the desk and started stripping.

Becky wasn’t surprised to see that he was already hard, but she was very glad when she saw him grab a bottle of lube and pour it all over his cock. Taking a risk, she reached out her hand, working the lube around his stiff member. Jake smiled and put some more lube on, he was getting very slippery and Becky was already grateful for that.

Jake handed her a towel and she wiped the lube off her hands. He took another towel and draped it over the oversized office chair that was situated near the desk and rolled it a bit closer.

“Turn around and have a seat,” Jake told her with a big grin on his face. Well, now she knew she would be sitting on his cock. She did as ordered and turned around and started to lower herself down. Jake moved the chair forward and reached out, grabbing her to help her down.

Becky’s hopes of some normal sex were quickly dashed when he positioned her butthole over his cock and started to pull her onto it. She felt silly to have that hope as her already tender bowels were once more being stretched by a large dick.